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Details

Stereochemistry ACHIRAL
Molecular Formula C20H25N3S
Molecular Weight 339.498
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PERAZINE

SMILES

CN1CCN(CCCN2C3=CC=CC=C3SC4=C2C=CC=C4)CC1

InChI

InChIKey=WEYVCQFUGFRXOM-UHFFFAOYSA-N
InChI=1S/C20H25N3S/c1-21-13-15-22(16-14-21)11-6-12-23-17-7-2-4-9-19(17)24-20-10-5-3-8-18(20)23/h2-5,7-10H,6,11-16H2,1H3

HIDE SMILES / InChI
Molecular Formula C20H25N3S
Molecular Weight 339.498
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: Description was created based on several sources, including http://www.ncbi.nlm.nih.gov/pubmed/12523495 and http://www.genome.jp/dbget-bin/www_bget?D01412

Perazine (Taxilan) is a moderate-potency typical antipsychotic of the phenothiazine class. Perazine is an older antipsychotic drug first introduced in the 1950s. It is suggested to have a low level of side effects (especially for movement disorders). Its use is regional and restricted to countries like Germany, Poland, the Netherlands and the former Yugoslavia. Perazine has being shown to be a potent inhibitor of human CYP1A2. It acts as a dopamine antagonist.

CNS Activity

Originator

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
Antagonist
2849
Cytochrome P450 2B, Rattus norvegicus
2
Target ID: Cytochrome P450 2B, Rattus norvegicus
Inhibitor
8504
 45.0 µM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8583
Taxilan

Approved Use

Taxilan is used in the treatment of schizophrenia
PubMed

PubMed

TitleDatePubMed
Neurologic complications in patients treated with lithium.
1988 Sep
An acute psychotic disorder caused by pefloxacin: a case report.
1996 Feb
Switching to amisulpride due to hepatic complications.
2002 May
The contribution of cytochrome P-450 isoenzymes to the metabolism of phenothiazine neuroleptics.
2002 Oct
Screening, library-assisted identification and validated quantification of fifteen neuroleptics and three of their metabolites in plasma by liquid chromatography/mass spectrometry with atmospheric pressure chemical ionization.
2003 Mar
Blood dyscrasias induced by psychotropic drugs.
2004 Mar
The metabolism of the piperazine-type phenothiazine neuroleptic perazine by the human cytochrome P-450 isoenzymes.
2004 May
Halogenation of drugs enhances membrane binding and permeation.
2004 May 3
Increased serum interleukin-1beta and interleukin-6 in elderly, chronic schizophrenic patients on stable antipsychotic medication.
2005 Jun
Analysis of phenothiazines in human body fluids using disk solid-phase extraction and liquid chromatography.
2005 Nov-Dec
Interactions between neuroleptics and CYP2C6 in rat liver--in vitro and ex vivo study.
2005 Nov-Dec
Metabolic profiling of CSF: evidence that early intervention may impact on disease progression and outcome in schizophrenia.
2006 Aug
[Trazodone for the treatment of behavioral and psychological symptoms of dementia (BPSD) in Alzheimer's disease: a retrospective study focused on the aggression and negativism in caregiving situations].
2006 Jun
Perazine and carbamazepine in comparison to olanzapine in schizophrenia.
2007
Simple and simultaneous determination for 12 phenothiazines in human serum by reversed-phase high-performance liquid chromatography.
2007 Jul 1
[Ischemic colitis without atherosclerosis?].
2007 Mar 30
The activity of cytochrome P450 CYP2B in rat liver during neuroleptic treatment.
2007 Sep-Oct
Typical and atypical antipsychotics--the misleading dichotomy. Results from the Working Group 'Drugs in Psychiatry' (AGATE).
2008
The effect of antipsychotic medication on sexual function and serum prolactin levels in community-treated schizophrenic patients: results from the Schizophrenia Trial of Aripiprazole (STAR) study (NCT00237913).
2008 Dec 22
Amisulpride plus valproate vs haloperidol plus valproate in the treatment of acute mania of bipolar I patients: a multicenter, open-label, randomized, comparative trial.
2008 Jun
Spectroscopic and electrochemical analysis of psychotropic drugs.
2009 Jan
Perazine at therapeutic drug concentrations inhibits human cytochrome P450 isoenzyme 1A2 (CYP1A2) and caffeine metabolism--an in vitro study.
2009 Sep-Oct
The role of CYP2D6 and TaqI A polymorphisms in malignant neuroleptic syndrome: two case reports with three episodes.
2010 Mar
[Perazine in the treatment of psychotic disorders--research review].
2010 May-Jun
Main contribution of the cytochrome P450 isoenzyme 1A2 (CYP1A2) to N-demethylation and 5-sulfoxidation of the phenothiazine neuroleptic chlorpromazine in human liver--A comparison with other phenothiazines.
2010 Oct 15
Patents

Patents

JP2008528532A
12

Sample Use Guides

In Vivo Use Guide
Curator's Comment: In acutely ill and severely disturbed patients 50 mg perazine at time-intervals of 30 minutes can be administered intramuscularly
The customary dose range recommended for this antipsychotic under in-patient conditions is 75-600 mg/day (maximum 1000 mg/day).
Route of Administration: Oral
In Vitro Use Guide
About 80% of basal human CYP1A2 activity was reduced by the therapeutic concentrations of perazine (5-10 uM).
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:24:35 GMT 2025
Edited
by admin
on Mon Mar 31 18:24:35 GMT 2025
Record UNII
8915147A2B
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PERAZINE
MI   WHO-DD  
Common Name English
PERAZINE [MI]
Preferred Name English
PROCHLORPERAZINE MALEATE IMPURITY B [EP IMPURITY]
Common Name English
10-(3-(4-METHYLPIPERAZIN-1-YL)PROPYL)PHENOTHIAZINE
Systematic Name English
Perazine [WHO-DD]
Common Name English
Classification Tree Code System Code
WHO-VATC QN05AB10
Created by admin on Mon Mar 31 18:24:35 GMT 2025 , Edited by admin on Mon Mar 31 18:24:35 GMT 2025
WHO-ATC N05AB10
Created by admin on Mon Mar 31 18:24:35 GMT 2025 , Edited by admin on Mon Mar 31 18:24:35 GMT 2025
NCI_THESAURUS C66883
Created by admin on Mon Mar 31 18:24:35 GMT 2025 , Edited by admin on Mon Mar 31 18:24:35 GMT 2025
Code System Code Type Description
RXCUI
8042
Created by admin on Mon Mar 31 18:24:35 GMT 2025 , Edited by admin on Mon Mar 31 18:24:35 GMT 2025
PRIMARY RxNorm
CAS
84-97-9
Created by admin on Mon Mar 31 18:24:35 GMT 2025 , Edited by admin on Mon Mar 31 18:24:35 GMT 2025
PRIMARY
WIKIPEDIA
Perazine
Created by admin on Mon Mar 31 18:24:35 GMT 2025 , Edited by admin on Mon Mar 31 18:24:35 GMT 2025
PRIMARY
NCI_THESAURUS
C81093
Created by admin on Mon Mar 31 18:24:35 GMT 2025 , Edited by admin on Mon Mar 31 18:24:35 GMT 2025
PRIMARY
FDA UNII
8915147A2B
Created by admin on Mon Mar 31 18:24:35 GMT 2025 , Edited by admin on Mon Mar 31 18:24:35 GMT 2025
PRIMARY
SMS_ID
100000079987
Created by admin on Mon Mar 31 18:24:35 GMT 2025 , Edited by admin on Mon Mar 31 18:24:35 GMT 2025
PRIMARY
DRUG CENTRAL
2100
Created by admin on Mon Mar 31 18:24:35 GMT 2025 , Edited by admin on Mon Mar 31 18:24:35 GMT 2025
PRIMARY
PUBCHEM
4744
Created by admin on Mon Mar 31 18:24:35 GMT 2025 , Edited by admin on Mon Mar 31 18:24:35 GMT 2025
PRIMARY
EPA CompTox
DTXSID6048628
Created by admin on Mon Mar 31 18:24:35 GMT 2025 , Edited by admin on Mon Mar 31 18:24:35 GMT 2025
PRIMARY
DRUG BANK
DB12710
Created by admin on Mon Mar 31 18:24:35 GMT 2025 , Edited by admin on Mon Mar 31 18:24:35 GMT 2025
PRIMARY
ChEMBL
CHEMBL1697766
Created by admin on Mon Mar 31 18:24:35 GMT 2025 , Edited by admin on Mon Mar 31 18:24:35 GMT 2025
PRIMARY
MESH
D010464
Created by admin on Mon Mar 31 18:24:35 GMT 2025 , Edited by admin on Mon Mar 31 18:24:35 GMT 2025
PRIMARY
EVMPD
SUB14811MIG
Created by admin on Mon Mar 31 18:24:35 GMT 2025 , Edited by admin on Mon Mar 31 18:24:35 GMT 2025
PRIMARY
MERCK INDEX
m8535
Created by admin on Mon Mar 31 18:24:35 GMT 2025 , Edited by admin on Mon Mar 31 18:24:35 GMT 2025
PRIMARY Merck Index
ECHA (EC/EINECS)
201-578-9
Created by admin on Mon Mar 31 18:24:35 GMT 2025 , Edited by admin on Mon Mar 31 18:24:35 GMT 2025
PRIMARY
Related Record Type Details
Structure of PERAZINE DIMALEATE
SALT/SOLVATE -> PARENT
Structure of PERAZINE DIMALONATE
SALT/SOLVATE -> PARENT
Structure of PERAZINE FENDIZOATE
SALT/SOLVATE -> PARENT
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Structure of PROCHLORPERAZINE MALEATE
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Structure of PROCHLORPERAZINE MALEATE
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Related Record Type Details
Structure of PERAZINE
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